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Explore Cortona

With magnificent panoramas, great old Italian architecture and some of the best food in the area, Cortona is the ideal destination for a romantic getaway or family vacation. The cobblestone streets, quaint buildings, and winding roads of Cortona make it one of the best walking towns in the area. If you are looking for great restaurants and shopping, be sure to check out Piazza Signorelli.

Here are a few additional suggestions of things to do in Cortona:

-Cooking Classes: Several hotels in the area offer half-day and full-day courses in the art of making traditional Italian dishes.

-The Archaeological Park: This route takes you along several Roman roads and past some beautiful architecture.

-Visit the Churches: Cortona is home to beautiful churches including the Duomo and Eremo Le Celle.

-Visit the Tombs: The Etruscan tombs are arguably the biggest attraction in the area.

-Palazzo Comunale: The town hall that was built in the early 13th century remains largely intact and offers guided tours.

Not surprisingly, many of the festivals in Cortona revolve around the amazing culinary attractions in the area. The biggest festival is the Sagra della Bisteca in August, which celebrates the steak from the local Chianina cows. The other main festival in the area is the Giostra dell'Archidado in May, an archery competition where representatives of the city's quarters compete while wearing historical costumes. The annual grape harvest, typically held in late September or early October, is another big event for Cortona.

Whether you want a condo with panoramic views of the vineyards out your front door, an apartment that's steps from all the major attractions and fine dining options, or a more secluded luxury villa in the outer parts of town, there's a vacation rental available to help you get the most out of your European getaway.

$509

Villa Fontocchio is situated at the foot of the Etruscan town of Cortona, in an enchanting location among vineyards and olive trees. Thanks to the careful restoration works, the charm of this typical Tuscan farmhouse, with its wooden beams and terracotta floors, has been preserved. A big gate leads into a spacious …

My favorite place in the world

Left on Oct 22, 2009 for a stay in July 2008

Villa Fontocchio is magical- the house is perfect- very difficult to find so many bathrooms and such spacious rooms. The view is amazing and the town is outstanding. It is perfectly situated with access to the hill town of Cortona and the business/shopping of Camuccia. We have stayed in this villa twice- once for 5 weeks and once for 3. The owner is wonderful, caring and conscientious and …

$319

Within walking distance of the centre of Cortona, Villa Valerie is a wonderful 500 year old Tuscan farmhouse, perched on a hill overlooking the Pergo valley, and rolling Tuscan hills with magnicent views. It has a unique charm and a dreamlike atmosphere that embraces its guests. The house for us is a great escape of …

$392

At the border between Umbria and Tuscany with stunning view to the Trasimeno Lake arises Villa Gosparini(600mt on see level). Villa Gosparini lies in an uncontaminated landscaped context, not far from Trasimeno shores and the most important art cities of Tuscany and Umbria. The recent reconstruction of the antique …

Fantastic Villa, amazing view

Left on Oct 11, 2012 for a stay in August 2012

We just had a great stay at Villa Gosparini.
We were 3 families, with 2 children each (18 month to 5.5 years-old). The size of the villa allowed us to keep privacy when necessary, and share very good times together, inside or on the various terrasses.
The house is very quiet, we had an amazing view on the lake, and the access to cities like Cortona, Perugia, Castiglione were very easy.
We …

$319

This luxury villa has been recently restored and tastefully customized is on the Tuscan / Umbrian border overlooking the one hand, the Tuscan hills in the direction of Cortona and the other side of Lake Trasimeno. A truly stunning lake view and hills awaits surrounded by colors and scents and magical, finding a way to…

Fabulous stay in a great location!!

Left on Jun 13, 2013 for a stay in March 2013

Stayed here in March while traveling with my best friend. Convenient to everything you want to see in Tuscany and Umbria. The ownwers are warm, kind and helpful. The accomodations are top notch. Beautiful setting and the house itself is georgeous. I will deffinately be back.

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$184 / night

$184

This imposing two-storey villa is set in stunning grounds, which have the quality of a park. Here you can feel sheltered and secluded in each separate area, including that of the pool. The spaciousness of both the exterior and interior easily accommodates a large group. Modern comforts have been succesfully integrated…

$858

Il Rifugio (The Refuge) is a respectfully restored seventeenth-century stone farmhouse/villa set on a Tuscan hillside surrounded by a centuries' old terraced olive grove and fifty six rolling acres of private property near the Etruscan citadel Cortona. Agriturismo Il Rifugio is the perfect vacation rental for families…

a wonderful Tuscan experience

Left on Feb 23, 2012 for a stay in July 2010

the house is large, well equipped, and comfortable for a reasonably large number of folks. Chuck and his wife can create a magnificent culinary experience as well. very large gourmet kitchen and ample dining space make this a joy.

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$463 / night

$463

Fonte al Vento is immersed in the green landscape of Tuscany, sitting on the typical terraces of the hilly countryside between olive groves, vineyards and other scented Mediterranean plants. It’s just a few steps from the Chiesa Monumentale di Santa Maria Nuova and Cortona’s Old Town, which can be reached in a few…

$235

Surrounded by the gentle hills which frame the medieval town of Cortona, Villa Eugenio will assure you a peaceful vacation in the heart of Tuscany. This beautiful 17th century Tuscan farmhouse has been painstakingly restored and turned into a warm and welcoming country house that can accommodate up to 10 people (8+2 …

Dream Vacation

Left on Sep 13, 2011 for a stay in May 2011

It is s beautiful, private estate. You will need a car to get anywhere, but otherwise the location is ideal. Beautiful views, quiet. Sign up for a dinner to be fixed for you- it was amazing! We added a second dinner once we had the first! The women who cooked where sweet and friendly.

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$175 / night

$175

Villa Berta is a spacious three-story villa surrounded by the greenery. It sleeps 12 people. From Villa Berta you will have a pleasant view of the Tuscan countryside. Villa Berta is 170 square meters (1830 square feet). It features a private swimming pool, a private garden and winter heating.
You will be roughly 3.5 …

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$494 / night

$494

If looking for a spacious Tuscan villa for rent that provides privacy and comfort, Villa Sogno is one of the best choices. The villa is located in a huge property, surrounded by green trees, well maintained grass and giant mountains, which nature lovers would adore. Your mind will be refreshed and you will feel …

$335 / night

$335

If you are looking for an exclusive location where time seems to stand still, welcome to Villa dei Ciliegi. Situated on the Cortona hill, with a breathtaking view on the valley, this villa will ensure you an unforgattable vacation. The house takes its name from the charming cherry tree-lined drive which takes you to …

One of my favourite place!

Left on Sep 30, 2010 for a stay in June 2009

I have been several times to Cortona and each time I stay at one of the villas owned by terretrusche.com. Charming place and warm hospitality. The location is a really a "slice of heaven". I loved the pool!!! I highly recommend staying in this property, it's perfect for 6/8. Enjoy the food and dinner in the patio in the summer nights. June is the perfect moment. Amazing!

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$190 / night

$190

Villa San Martino is set in a delightful position among extensive grounds overlooking the countryside. The swimming pool is surrounded by olive trees and lush gardens.
The nearest town is Cortona, famous for its ancient backgrounds, home town of famous painter Luca Signorelli. Recently it has been the set for the …

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$1,119 / night

$1,119

The villa is located in a superb area to conveniently visit most of the attractions of Tuscany and North of Umbria being right at the border between the two regions.
The villa is situated 20 minutes from Cortona, 20 minutes from Arezzo, 20 minutes from Perugia, 40 minutes from Siena and one hour and a half from …

$319

Villa La Pergola is an authentic private villa in Tuscany, very close to the Etruscan town of Cortona. La Pergola is situated in a cosy village consisting of two other villas each with private swimming pool. The patio, decorated with elegant garden furniture, has a scenic view over the well-manicured garden with pool …

nice home in beautiful location

Left on Nov 10, 2010 for a stay in October 2010

Stayed one week 3rd week of october. Weather was good all week, but cool at night. We used nice fireplace for heat in the mornings and evenings (chose not to turn on optional-cost heating). We used 3 bedrooms, each with its own separate bath and all were nice. Kitchen is small but ok. Dining area beside fireplace is country table - good atmosphere for family gathering. We used the place …

$2,046

A stay at Villa Laura is your chance to live out your own Under the Tuscan Sun. This ten-bedroom property played the role of the villa Bramasole in the film. Just as the fictional villa is given a makeover, Villa Laura was recently renovated with an eye to traditional style and touches of quiet luxury. Airy and …

Our fantastic family vacation in Tuscany

Left on Mar 15, 2013 for a stay in March 2013

Luxury Retreat exceeded our expectations. We were considering joining a vacation club but after using Luxury Retreat.....we realize that there is no need for it. They have been trust worthy, responsibleb & available. Villa Bramasole was truly a wonderful expierence for our family.....now if only they could adjust the weather forecast....lol. We are already considering going back next summer. …

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$252 / night

$252

Villa Le Corchie is a charming villa located in a quiet and panoramic position in one of the most scenic areas of the hills surrounding Cortona.
Thanks to a careful restoration completed in September 2011, the old country house dating back to the fifteenth century, was transformed into a beautiful private independent…

$400

Villa Borgonuovo is a beautiful farmhouse, which has been recently restored, according to the typical Tuscan style, and equipped with all comforts. The villa lies at Cortona's feet, only 15 minutes away from the town centre. The villa is a perfect example of the traditional Tuscan farmhouse: ample loggia, huge halls, …

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$198 / night

$198

Villa Angiola dwells on the hills that surround the amazing Cortona region with its historic heritage and breathtaking landscapes. A 17th century country home, now Villa Angiola, was converted into a comfortable venue that can accommodate up to 10 people in its beautiful quarters. Built in stone, the villa exhibits a …

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$272 / night

$272

Positioned amidst one of the prettiest spots surrounding Cortona, Villa Acacia is a quiet, peaceful and charming villa has been recently restored in September 2011. An historic country house originally built in the fifteenth century the villa has been carefully restored to its original beauty without compromising on …

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$504 / night

$504

Villa Casale Girifalco, 16th century, is a charming country house, located on an extensive ground (nearly 5 hectares) with a stunning view of the Valdichiana valley. Perched on the terraced slopes of olive groves, it guarantees you complete privacy and tranquility, while at the same time being at walking distance from…

Magical tuscany at Casale Girifalco

Left on Oct 29, 2011 for a stay in October 2011

Our month in Tuscany was a dream come true. The villa was even better than the pictures. Manuella and her right hand man Carlo always had a ready smile and cheerful response to our questions. Manuella's first restaurant recommendation led us to our favorite tuscan restaurant, la Bucaccia, in Cortona. Carlo even gave us an apprenticeship in olive harvesting. We loved the walks through the orchards…

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$320 / night

$320

This luxury Cortona country cottage for 8 people offers a peaceful retreat to rural Italy. It is situated in a wonderful position overlooking the surrounding land.
Additional amenities include: heating.

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$298 / night

$298

A large and traditional villa for 8, with four bedrooms, a fully equipped kitchen, private garden with swimming pool, BBQ area and playground, and stunning views of the surroundings.
Additional amenities include: heating.

$614

Fonte al Vento is a detached villa wisely set in a large property against a breathtaking landscape that includes an additional accommodation facilities. Each one has its own private garden, swimming pool and spaces for exclusive use to completely respect the privacy of our guests.
The Villa is placed in the beautiful…

Will Never Stay anywhere else in Cortona!

Left on Jul 03, 2014 for a stay in June 2014

The Villa was the perfect place to travel the Tuscany area from! Everything about The Villa was exceptional...views, comfort, accommodations, and hosts (Silvia & Francesco). It fit 6 of us very comfortably, and would fit 8 for sure. Each spacious bedroom has its own fully accommodated, attached bathroom. It is peaceful and quiet! Silvia was extremely responsive with the booking and all the …

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$204 / night

$204

“That upwanding road between wheat, sunflower and green hay takes”….700th refuge in the country of Conti Serristori in wich the old antique walls are now open to all those who wish to enjoy the countryside. You are surrounded by splendid hills, like magic together with the hot Tuscan sunthey merge to give you a …

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$768 / night

$768

Nature, culture, history and traditions meet in this splendid villa in Cortona, in the Tuscan region. Large and with an adjacent cottage for two, this villa is perfect for big groups.
Additional amenities include: pets considered, heating.

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$717 / night

$717

A five double bedroomed villa with private pool offering its guests complete luxury.
Villa Manzano is a beautifully restored retaining much of its original character and tastefully furnished with antiques and original paintings to a very high standard, with no expense spared.
Only a fifteen minute drive to the …

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$149 / night

$149

Villa Il Roseto is located in a beautiful panoramic position, where it dominates both Tuscany and Umbria, a few kilometers from the ancient Etruscan town of Cortona.
Villa Il Roseto will allow you to easily reach the most beautiful cities of Tuscany and Umbria, but at the same time you'll enjoy a holiday in an …

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$224 / night

$224

Villa Rosmarino is a place of peace and tranquility, situated in an elevated position which offers an unparalleled view of Cortona and the entire Valdichiana. The villa is nestled in the beautiful woods of the hill of Cortona, in a healthy and fresh ambience thanks to the tall pine trees and firs, accompanied by …

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$486 / night

$486

The structure of this beautiful villa dates back to 1800s. The house was fully and lovingly restored in 1998 and measures approximately 142 square metres. The Villa Melograno is located on a family estate, where there are 2 other villas, both also used for vacation rentals.andnbsp Villa Melograno andnbspis built …

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$169 / night

$169

Villa Verbena combines privacy and convenience in a single solution: the villa is in fact located in the small town of Camucia, at the foot of the famous and beautiful Cortona, allowing its guests to reach all the services they need within walking distance (station, supermarkets, services ), but at the same time it is…

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$196 / night

$196

RECEPTIVE STRUCTURE. I Mandorli is a typical Tuscan stone farmhouse, located a few kilometres from Cortona, a charming little town in the heart of Tuscany. The property is part of a farm estate of about 6 hectares where the owners produce olive oil and wine which they share with their guests and friends. The house was…

$25 / night

$25

Rasina is situated in a stunning position at 500m of altitude over the Tuscan hills of Cortona, which give the house a fantastic and unique panoramic view. Rasina house is an ancient rural house that has been recently restored strictly using traditional materials, in accordance with the typical building typologies of …

Views to die for...

Left on Dec 02, 2014 for a stay in September 2014

This villa is so much more than the pictures lead you to believe. It's a pain to get to but I think that just adds to the charm. The views from the villa are fantastic and as you can imagine it's seclusion means complete and utter silence.

All the rooms are huge and the facilities are great. It could do with a new sofa or two but that's pretty much my only complaint.

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$144 / night

$144

It’s a characteristic middle age tower, it’s origins can be leaded up around the year 1000 A.C. (The building is rises nearby the Etruscan town of Cortona). We wanted to give it the name of Dardano by the way the legend tells that this mythological character was the founder of Cortona and that from here he left to…

$320

Moses' Palace, just a few steps away from the house you will find everything that is wonderful about Italy - the beautiful and lively piazzas, great shopping, bars and restaurants, cultural events, churches and art treasures.
It is a typical 3 floors palace built few century ago,
the street floor has a large entrance…

Dream Vacation

Left on Mar 21, 2012 for a stay in September 2011

Cortona is a beautiful place and the location on Moses Palace allowed us to walk to the piazza every day and night. Shops and wonderful restaurants were all around us. Right next to a beautiful church and could walk to see the house in Under the Tuscan Sun! The place is set up so nice with bedrooms on three different floors--so their is privacy and multiple bathrooms. The location couldn't be…

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$191 / night

$191

Stone-built farmhouse that has recently been restored with great care and is situated in the hills approximately three kiliometers from Cortona.
The property is situated in a well reserved country place but not remote, very near to all necessity. The Villa is divided into two indipendent units and there are five …

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$392 / night

$392

This is a property of great charm immersed in the relaxing panoramic countryside around Cortona.
The original farmhouse dates back to the 17th century and has been recently restored maintaining the typical features of the Tuscan villas: stone walls, wood beams and terracotta floors for a homely rustic style.The …

$341

Tucked under the ancient Etruscan walls of Cortona, the recently restored old stone Villa Topazio lies up on the hill and is part of a beatiful Renaissance Villa. From Villa Topazio one can admire the splendid view of the Valdichiana completely surrounded by olive groves which produce some of our excellent local extra…

Welcoming, comfortable, beautiful property high in the hills a short distance from the town of Corto

Left on Oct 04, 2011 for a stay in September 2011

There were three couples and we had a fabulous week at this villa. One in our group has some walking limitations and while she managed, I wouldn't recommend this location for someone with disabilities. The owners were very gracious and accommodating and attended to all our needs. Great location for side trips to Montepulciano, Pienza, Panzano, Greve and more. You must navigate some steep …

A wonderful family holiday in a beautiful setting and great loca

Left on Oct 30, 2009 for a stay in September 2008

We rented Villa Le Contesse in Cortona for two weeks last September. We invited family and friends to join us. The house is romantically beautiful in a "shabby chic" way. There were plenty of bedrooms and bathroom. The highlight was the cook,Camela, who prepared delicious, classic Tuscan meals. We mostly ate outside on the courtyard in front of the house. The pool was delighful. We took day…

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$274 / night

$274

PRIVATE STRUCTURE. With a 180° view of the Carpina Valley - an area set between the Upper Tiber Valley and the Umbria-Marche Apennine ridge where the Carpina river and its tributaries determine the succession of hills with alternating dense oak forests, vineyards and olive groves - reaching to the horizon, with the …

$525

This exclusive villa that dominates a huge landed property offers magnificent views of the surrounding countryside, and is situated on the gentle rolling hills of the Tuscan/Umbrian border between Montepulciano, Cortona and Lake Trasimeno. This is a central location of southern Tuscany; Siena is only 50 minutes by car…

our daughter's wedding, was fantastic

Left on Jan 20, 2014 for a stay in August 2013

Hi Sabrina, I am sorry not to send feedback sooner, regarding our stay at Villa Vera. However our trip to Cortona for our daughter's wedding, was fantastic. The villa itself was well equipped, the furniture around the pool was new, along with the outside barbeque and oven. The pool was clean and well mantained. The separate annexes made sharing with a large group easier, with regards catering and…

$399

This luxury villa, surrounded by a gorgeous and impressive garden, has been recently restored with great care of details and with respect to Tuscan tradition. What a great location! The villa is ideally located close to village and services offering at the same time absolute privacy and quietness. Villages are within …

Really friendly and helpful owners

Left on Aug 10, 2012 for a stay in June 2012

We have been renting villas in Italy for a number of years. What was very impressive about this villa was how helpful the owners. Paolo and Firella were. When we did have a problem they reacted immediately to put matters right. They were exceptional hosts and they made our holiday an exceptional experience.

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$1,599 / night

$1,599

Set in the Tuscan hills between Cortona and Mercatale, this exquisite manor house is the ideal retreat for those wishing to enjoy idyllic and peaceful surroundings in extreme comfort. Set within its own meadows and olive groves, a private lake and numerous woodland walks, it is still within easy reach of many of the …

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$601 / night

$601

A luxury villa built and restored over two floors with six bedrooms and six en-suite bathrooms in a fabulous countryside location with a fabulous swimming pool, situated in the heart of Tuscany in a splendid hillside position with stunning views of the Tuscan vines and olives along with the green forests of Monte …

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$320 / night

$320

Villa Del Sole is the perfect place for an unforgettable experience! This magnificent property is situated in the heart of the hills of Cortona, in an extremely panoramic position that will offer your eyes all the spectacular splendor of the lush Tuscan countryside.
The villa has spacious and beautiful outdoor spaces …

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$1,998 / night

$1,998

If your dream Tuscan vacation is a rural idyll, Casale di Reschio may be your dream come true. Tucked into the hills between Cortona and Mercatale, the seven-bedroom stone house has stunning views of the countryside, inviting outdoor spaces and luxurious, welcoming interiors. Though it’s located on 84 acres of …

$884

In the 18th century, Villa Tegognano was a country retreat for an aristocratic family. Today, this renovated four-bedroom manor house is still a quiet getaway, but with modern amenities. With commanding views of the countryside near Cortona, the villa’s location is unforgettable, and its cozy, traditional interiors …

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$204 / night

$204

Extending over the ground and top floors of part of a large villa, this superior accommodation provides more than just a touch of distinctive style and class! It comprises all modern comforts, while retaining many original Tuscan design features and elegant traditional furnishings. As the owners live at the rear of …

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$464 / night

$464

Independent four bedroom villa-Cortona
Villa Wind is a fabulous private and newly restored villa, in the midst of the beautiful Tuscan hills, with amazing views and a superb swimming pool. There is ample space for relaxing and eating alfresco, with vineyards and olive groves surrounding the villa, yet it is only a …

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$528 / night

$528

Independent five bedroom villa-Cortona
Villa Wind is a fabulous private villa, with a separate Cottage, Wind O just below it. It is a newly restored villa, in the midst of the beautiful Tuscan hills, with amazing views and a superb swimming pool. There is ample space for relaxing and eating alfresco, with vineyards…

About Cortona

With magnificent panoramas, great old Italian architecture and some of the best food in the area, Cortona is the ideal destination for a romantic getaway or family vacation. The cobblestone streets, quaint buildings, and winding roads of Cortona make it one of the best walking towns in the area. If you are looking for great restaurants and shopping, be sure to check out Piazza Signorelli.

Here are a few additional suggestions of things to do in Cortona:

-Cooking Classes: Several hotels in the area offer half-day and full-day courses in the art of making traditional Italian dishes.

-The Archaeological Park: This route takes you along several Roman roads and past some beautiful architecture.

-Visit the Churches: Cortona is home to beautiful churches including the Duomo and Eremo Le Celle.

-Visit the Tombs: The Etruscan tombs are arguably the biggest attraction in the area.

-Palazzo Comunale: The town hall that was built in the early 13th century remains largely intact and offers guided tours.

Not surprisingly, many of the festivals in Cortona revolve around the amazing culinary attractions in the area. The biggest festival is the Sagra della Bisteca in August, which celebrates the steak from the local Chianina cows. The other main festival in the area is the Giostra dell'Archidado in May, an archery competition where representatives of the city's quarters compete while wearing historical costumes. The annual grape harvest, typically held in late September or early October, is another big event for Cortona.

Whether you want a condo with panoramic views of the vineyards out your front door, an apartment that's steps from all the major attractions and fine dining options, or a more secluded luxury villa in the outer parts of town, there's a vacation rental available to help you get the most out of your European getaway.

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